Hydrazine → ethyl 2-[P-ethyl-2-hydroxyamino-5-(2-chloro-4-trifluoromethylphenoxy)phenylphosphinyloxyimino]propionate

HRID 1980457Notes

Reaction equation

HRID 1980457 reaction equation
[CH2:1]([P:3]([C:14]1[CH:19]=[C:18]([O:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:22]=2[Cl:31])[CH:17]=[CH:16][C:15]=1[N+:32]([O-])=[O:33])([O:5][N:6]=[C:7]([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:4])[CH3:2].NN>O1CCCC1.[Rh]>[CH2:1]([P:3]([C:14]1[CH:19]=[C:18]([O:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:29])([F:30])[F:28])=[CH:23][C:22]=2[Cl:31])[CH:17]=[CH:16][C:15]=1[NH:32][OH:33])([O:5][N:6]=[C:7]([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:4])[CH3:2]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 86740017ethyl 2-[P-ethyl-2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenylphosphinyloxyimino]propionate

Product 1

HCID 86740016ethyl 2-[P-ethyl-2-hydroxyamino-5-(2-chloro-4-trifluoromethylphenoxy)phenylphosphinyloxyimino]propionate

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-[P-ethyl-2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenylphosphinyloxyimino]propionate (500 mg) in tetrahydrofuran (10 ml) is added hydrazine (1 eq.) and 5% rhodium on activated charcoal (50 mg) at 15°-25°, with stirring for 2 hours. The reaction is then filtered and the filtrate is diluted with methylene chloride, washed, dried and concentrated to dryness to give ethyl 2-[P-ethyl-2-hydroxyamino-5-(2-chloro-4-trifluoromethylphenoxy)phenylphosphinyloxyimino]propionate.

Workup

  1. filtrationThe reaction is then filtered
  2. additionthe filtrate is diluted with methylene chloride
  3. washwashed
  4. customdried
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-40e54f80e93c489bb294406d7e2b5d61
Source dataset
uspto-grants-1985_04
Patent number
US04509970

Reaction notes

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